In vitro biotransformation of decabromodiphenyl ether (BDE-209) and Dechlorane Plus flame retardants: A case study of ring-billed gull breeding in a pollution hotspot in the St. Lawrence River, Canada

Environment International

Volumn 55, Issue , 2013, Pages 101-108

  Chabot Giguère, Bernice ^a   Letcher, Robert J ^b   Verreault, Jonathan ^a  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

^b CARLETON UNIVERSITY   (Canada)

Author keywords

Biotransformation; Bird; Deca BDE; Dechlorane Plus; Emerging flame retardant; In vitro assay

Indexed keywords

BIOCONVERSION; BIRDS; DEHALOGENATION; ETHERS; FISH; ISOMERS; METABOLISM; OCEAN HABITATS; RIVER POLLUTION;

BIOTRANSFORMATION; DECA-BDE; DECHLORANE PLUS; EMERGING FLAME RETARDANTS; IN-VITRO ASSAYS;

FLAME RETARDANTS;

DECABROMODIPHENYL ETHER; DIPHENYL ETHER; ETHOXYRESORUFIN DEETHYLASE; FLAME RETARDANT; UNCLASSIFIED DRUG;

BIOASSAY; BIOTRANSFORMATION; BREEDING; CONCENTRATION (COMPOSITION); ENZYME; EXPERIMENTAL STUDY; METABOLISM; SEABIRD;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL MONITORING; BIOTRANSFORMATION; BIRD; BREEDING; CANADA; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DEBROMINATION; DEHALOGENATION; ENZYME ACTIVITY; ENZYME ASSAY; FEMALE; GEOGRAPHIC DISTRIBUTION; IN VITRO STUDY; ISOMER; LARUS DELAWARENSIS; LIVER LEVEL; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL;

CANADA; MONTREAL; QUEBEC [CANADA]; SAINT LAWRENCE RIVER;

EID: 84875684292     PISSN: 01604120     EISSN: 18736750     Source Type: Journal    
DOI: 10.1016/j.envint.2013.02.008     Document Type: Article

References (55)

1. Birnbaum L.S., Staskal D.F. Brominated flame retardants: cause for concern?. Environ Health Perspect 2004, 112:9-17.
2. Boon J.P., van der Meer J., Allchin C.R., Law R.J., Klungsoyr J., Leonards P.E., et al. Concentration-dependent changes of PCB patterns in fish-eating mammals: structural evidence for induction of cytochrome P450. Arch Environ Contam Toxicol 1997, 33:298-311.
3. Boon J.P., Lewis W.E., Goksoyr A. Immunochemical and catalytic characterization of hepatic microsomal cytochrome P450 in the sperm whale (Physeter macrocephalus). Aquat Toxicol 2001, 52:297-309.
4. Borlakoglu J.T., Wilkins J.P. Correlations between the molecular structures of polyhalogenated biphenyls and their metabolism by hepatic microsomal monooxygenases. Comp Biochem Physiol C 1993, 105:113-117.
5. BSEF About deca-BDE Available at, [Last accessed on Nov. 13th]. http://www.bsef.com/our-substances/deca-bde/about-deca-bde.
6. Chen G., Bunce N.J. Polybrominated diphenyl ethers as Ah receptor agonists and antagonists. Toxicol Sci 2003, 76:310-320.
7. Chen D., Hale R.C. A global review of polybrominated diphenyl ether flame retardant contamination in birds. Environ Int 2010, 36:800-811.
8. Chen D., Hale R.C., Watts B.D., La Guardia M.J., Harvey E., Mojica E.K. Species-specific accumulation of polybrominated diphenyl ether flame retardants in birds of prey from the Chesapeake Bay region, USA. Environ Pollut 2010, 158:1883-1889.
9. Chen D., Letcher R.J., Burgess N.M., Champoux L., Elliott J.E., Hebert C.E., et al. Flame retardants in eggs of four gull species (Laridae) from breeding sites spanning Atlantic to Pacific Canada. Environ Pollut 2012, 168:1-9.
10. Erratico C.A., Moffatt S.C., Bandiera S.M. Comparative oxidative metabolism of BDE-47 and BDE-99 by rat hepatic microsomes. Toxicol Sci 2011, 123:37-47.
11. Gauthier L.T., Letcher R.J. Isomers of Dechlorane Plus flame retardant in the eggs of herring gulls (Larus argentatus) from the Laurentian Great Lakes of North America: temporal changes and spatial distribution. Chemosphere 2009, 75:115-120.
12. Gauthier L.T., Hebert C.E., Weseloh D.V., Letcher R.J. Current-use flame retardants in the eggs of herring gulls (Larus argentatus) from the Laurentian Great Lakes. Environ Sci Technol 2007, 41:4561-4567.
13. Gauthier L.T., Hebert C.E., Weseloh D.V., Letcher R.J. Dramatic changes in the temporal trends of polybrominated diphenyl ethers (PBDEs) in herring gull eggs from the Laurentian Great Lakes: 1982-2006. Environ Sci Technol 2008, 42:1524-1530.
14. Gentes M.-L., Letcher R.J., Caron-Beaudoin É., Verreault J. Novel Flame retardants in urban-feeding ring-billed gulls from the St-Lawrence River, Canada. Environ Sci Technol 2012, 46:9735-9744.
15. Guerra P., Fernie K., Jimenez B., Pacepavicius G., Shen L., Reiner E., et al. Dechlorane Plus and related compounds in Peregrine Falcon (Falco peregrinus) Eggs from Canada and Spain. Environ Sci Technol 2011, 45:1284-1290.
16. Hakk H., Letcher R.J. Metabolism in the toxicokinetics and fate of brominated flame retardants- a review. Environ Int 2003, 29:801-828.
17. Hardy M.L. A comparison of the properties of the major commercial PBDPO/PBDE product to those of major PBB and PCB products. Chemosphere 2002, 46:717-728.
18. He J., Robrock K.R., Alvarez-Cohen L. Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs). Environ Sci Technol 2006, 40:4429-4434.
19. Kannan N., Reusch T.B., Schulz-Bull D.E., Petrick G., Duinker J.C. Chlorobiphenyls: model compounds for metabolism in food chain organisms and their potential use as ecotoxicological stress indicators by application of the metabolic slope concept. Environ Sci Technol 1995, 29:1851-1859.
20. Kennedy S.W., Jones S.P. Simultaneous measurement of cytochrome P4501A catalytic activity and total protein concentration with a fluorescence plate reader. Anal Biochem 1994, 222:217-223.
21. Kierkegaard A., Balk L., Tjärnlund U., de Wit C.A., Jansson B. Dietary uptake and biological effects of decabromodiphenyl ether in rainbow trout (Oncorhynchus mykiss). Environ Sci Technol 1999, 33:1612-1617.
22. La Guardia M.J., Hale R.C., Harvey E. Detailed polybrominated diphenyl ether (PBDE) congener composition of the widely used penta-, octa-, and deca-PBDE technical flame-retardant mixtures. Environ Sci Technol 2006, 40:6247-6254.
23. La Guardia M.J., Hale R.C., Harvey E. Evidence of debromination of decabromodiphenyl ether (BDE-209) in biota from a wastewater receiving stream. Environ Sci Technol 2007, 41:6663-6670.
24. Leslie H.A., Leonards P.E., Shore R.F., Walker L.A., Bersuder P.R., Morris S., et al. Decabromodiphenylether and hexabromocyclododecane in wild birds from the United Kingdom, Sweden and The Netherlands: Screening and time trends. Chemosphere 2011, 82:88-95.
25. Lindberg P., Sellstrom U., Haggberg L., de Wit C.A. Higher brominated diphenyl ethers and hexabromocyclododecane found in eggs of peregrine falcons (Falco peregrinus) breeding in Sweden. Environ Sci Technol 2004, 38:93-96.
26. Liu Y.T., Hao H.P., Liu C.X., Wang G.J., Xie H.G. Drugs as CYP3A probes, inducers, and inhibitors. Drug Metab Rev 2007, 39:699-721.
27. McKinney M.A., De Guise S., Martineau D., Beland P., Arukwe A., Letcher R.J. Biotransformation of polybrominated diphenyl ethers and polychlorinated biphenyls in beluga whale (Delphinapterus leucas) and rat mammalian model using an in vitro hepatic microsomal assay. Aquat Toxicol 2006, 77:87-97.
28. McKinney M.A., Dietz R., Sonne C., De Guise S., Skirnisson K., Karlsson K., et al. Comparative hepatic microsomal biotransformation of selected PBDEs, including decabromodiphenyl ether, and decabromodiphenyl ethane flame retardants in Arctic marine-feeding mammals. Environ Toxicol Chem 2011, 30:1506-1514.
29. McNabb F.M.A. Thyroid hormones: production, storage, and release by the thyroid gland. Thyroid hormones 1992, 3:21-48. Prentice Hall, Englewood Cliffs, New-Jersey, USA, [chap.].
30. Morck A., Hakk H., Orn U., Klasson Wehler E. Decabromodiphenyl ether in the rat: absorption, distribution, metabolism, and excretion. Drug Metab Dispos 2003, 31:900-907.
31. Munoz-Arnanz J., Saez M., Hiraldo F., Baos R., Pacepavicius G., Alaee M., et al. Dechlorane plus and possible degradation products in white stork eggs from Spain. Environ Int 2011, 37:1164-1168.
32. Noyes P.D., Hinton D.E., Stapleton H.M. Accumulation and debromination of decabromodiphenyl ether (BDE-209) in juvenile fathead minnows (Pimephales promelas) induces thyroid disruption and liver alterations. Toxicol Sci 2011, 122:265-274.
33. Pacyniak E.K., Cheng X., Cunningham M.L., Crofton K., Klaassen C.D., Guo G.L. The flame retardants, polybrominated diphenyl ethers, are pregnane X receptor activators. Toxicol Sci 2007, 97:94-102.
34. Ren G., Yu Z., Ma S., Li H., Peng P., Sheng G., et al. Determination of Dechlorane Plus in serum from electronics dismantling workers in South China. Environ Sci Technol 2009, 43:9453-9457.
35. Ross P.S., Couillard C.M., Ikonomou M.G., Johannessen S.C., Lebeuf M., Macdonald R.W., et al. Large and growing environmental reservoirs of Deca-BDE present an emerging health risk for fish and marine mammals. Mar Pollut Bull 2009, 58:7-10.
36. Shen M., Cheng J., Wu R., Zhang S., Mao L., Gao S. Metabolism of polybrominated diphenyl ethers and tetrabromobisphenol A by fish liver subcellular fractions in vitro. Aquat Toxicol 2012, 114-115:73-79.
37. Soderstrom G., Sellstrom U., de Wit C.A., Tysklind M. Photolytic debromination of decabromodiphenyl ether (BDE 209). Environ Sci Technol 2004, 38:127-132.
38. Stapleton H.M., Alaee M., Letcher R.J., Baker J.E. Debromination of the flame retardant decabromodiphenyl ether by juvenile carp (Cyprinus carpio) following dietary exposure. Environ Sci Technol 2004, 38:112-119.
39. Stapleton H.M., Brazil B., Holbrook R.D., Mitchelmore C.L., Benedict R., Konstantinov A., et al. In vivo and in vitro debromination of decabromodiphenyl ether (BDE 209) by juvenile rainbow trout and common carp. Environ Sci Technol 2006, 40:4653-4658.
40. Stapleton H.M., Kelly S.M., Pei R., Letcher R.J., Gunsch C. Metabolism of polybrominated diphenyl ethers (PBDEs) by human hepatocytes in vitro. Environ Health Perspect 2009, 117:197-202.
41. Sverko E., Tomy G.T., Marvin C.H., Zaruk D., Reiner E., Helm P.A., et al. Dechlorane Plus levels in sediment of the Lower Great Lakes. Environ Sci Technol 2008, 42:361-366.
42. Sverko E., Tomy G.T., Reiner E.J., Li Y.F., McCarry B.E., Arnot J.A., et al. Dechlorane plus and related compounds in the environment: a review. Environ Sci Technol 2011, 45:5088-5098.
43. Tomy G.T., Thomas C.R., Zidane T.M., Murison K.E., Pleskach K., Hare J., et al. Examination of isomer specific bioaccumulation parameters and potential in vivo hepatic metabolites of syn- and anti-Dechlorane Plus isomers in juvenile rainbow trout (Oncorhynchus mykiss). Environ Sci Technol 2008, 42:5562-5567.
44. UNEP The 9 new POPs: An introduction to the nine chemicals added to the Stockholm Convention by the Conference of the Parties at its fourth meeting 2010, [Available at: http://chm.pops.int/Programmes/NewPOPs/Publications/tabid/695/language/en-US/Default.aspx. Last accessed on Nov. 13th, 2012].
45. USEPA High production volume challenge program 2011, [Available at: http://www.epa.gov/hpv/index.htm. Last accessed on June. 18th, 2012].
46. Van den Steen E., Covaci A., Jaspers V.L., Dauwe T., Voorspoels S., Eens M., et al. Accumulation, tissue-specific distribution and debromination of decabromodiphenyl ether (BDE 209) in European starlings (Sturnus vulgaris). Environ Pollut 2007, 148:648-653.
47. Venier M., Wierda M., Bowerman W.W., Hites R.A. Flame retardants and organochlorine pollutants in bald eagle plasma from the Great Lakes region. Chemosphere 2010, 80:1234-1240.
48. Verreault J., Gabrielsen G.W., Chu S., Muir D.C., Andersen M., Hamaed A., et al. Flame retardants and methoxylated and hydroxylated polybrominated diphenyl ethers in two Norwegian Arctic top predators: glaucous gulls and polar bears. Environ Sci Technol 2005, 39:6021-6028.
49. Verreault J., Maisonneuve F., Dietz R., Sonne C., Letcher R.J. Comparative hepatic activity of xenobiotic-metabolizing enzymes and concentrations of organohalogens and their hydroxylated analogues in captive Greenland sledge dogs (Canis familiaris). Environ Toxicol Chem 2009, 28:162-172.
50. Verreault J., Letcher R.J., Sonne C., Dietz R. In vitro metabolism of polychlorinated biphenyls and cytochrome P450 monooxygenase activities in dietary-exposed Greenland sledge dogs. Comp Biochem Physiol C Toxicol Pharmacol 2009, 150:91-100.
51. Wang Y., Liu H., Zhao C., Liu H., Cai Z., Jiang G. Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners. Environ Sci Technol 2005, 39:4961-4966.
52. Wiseman S.B., Wan Y., Chang H., Zhang X., Hecker M., Jones P.D., et al. Polybrominated diphenyl ethers and their hydroxylated/methoxylated analogs: environmental sources, metabolic relationships, and relative toxicities. Mar Pollut Bull 2011, 63:179-188.
53. Xian Q., Siddique S., Li T., Feng Y.L., Takser L., Zhu J. Sources and environmental behavior of dechlorane plus - a review. Environ Int 2011, 37:1273-1284.
54. Zhang X.L., Luo X.J., Liu H.Y., Yu L.H., Chen S.J., Mai B.X. Bioaccumulation of several brominated flame retardants and dechlorane plus in waterbirds from an e-waste recycling region in South China: associated with trophic level and diet sources. Environ Sci Technol 2011, 45:400-405.
55. Zheng J., Wang J., Luo X.J., Tian M., He L.Y., Yuan J.G., et al. Dechlorane Plus in human hair from an e-waste recycling area in South China: comparison with dust. Environ Sci Technol 2010, 44:9298-9303.